ethyl 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,6-difluoro-5-hydroxyhex-2(E)-enoate | 1574159-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,6-difluoro-5-hydroxyhex-2(E)-enoate
• CAS: 1574159-03-7
• 化学式: C₁₇H₁₇F₂NO₅
• 分子量: 353.322
• InChiKey: AVVKYYXQRBZQTQ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4-difluoro-3-hydroxy-butyraldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 以52%的产率得到ethyl 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,6-difluoro-5-hydroxyhex-2(E)-enoate
  参考文献：
  名称：

  Synthesis of enantiomerically pure 4-polyfluoromethyl-4-hydroxy-homoprolines by intramolecular cyclization of 6-amino-5-polyfluoromethyl-hex-2-enoic acids

  摘要：

  An effective route to racemic and enantiopure 4-polyfluoromethyl-4-hydroxy-homoprolines was developed based on readily available 2-alkoxyvinyl-polyfluoromethyl ketones. Key step of the synthesis was a diastereoselective heterocyclization of 6-amino-5-polyfluoromethyl-hex-2-enoic acids under acidic conditions. The absolute configuration of the stereogenic centers was determined by X-ray. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.01.001